When Brigitte Barren Williams realized Donald Trump had won the presidential election, “it felt like somebody let the air out of a balloon,” she said. Her brother, David Barren, is locked up at a federal prison in West Virginia, serving life plus 20 years on federal drug conspiracy charges. Now in his 50s, Barren has served almost 10 years of his sentence — the minimum portion required before he is eligible to seek a commutation under President Obama’s clemency initiative.

Tens of thousands of people convicted of nonviolent federal drug crimes have sought mercy under the program, which was announced in April 2014. Obama ramped up his commutations in advance of the election, and Williams prayed with each clemency announcement that her brother’s name might be on the list. After the last round came out, on November 4, Williams was forced to hope that if Obama didn’t grant her brother clemency, perhaps his successor might.

But the chances of that almost certainly dissolved on election night. Trump has called the clemency recipients “bad dudes,” warning one audience this summer that “they’re walking the streets. Sleep tight, folks.” After winning the White House on such fearmongering rhetoric — and promptly naming a white supremacist to his cabinet — Trump chose Alabama Sen. Jeff Sessions as his attorney general, an opponent of criminal justice reform and defender of mandatory minimums. There is little reason to believe President Trump will show mercy to people like Barren.

Yet Williams remains steadfast in her belief that her brother will come home. “We are a family of very strong faith,” she said. Besides, her fight does not end with his freedom. There are too many others in his position. “We have to continue making sure people care.”

Williams spoke over the phone from Washington, D.C., where she had traveled from Pittsburgh for a series of public events under the theme “Hope for the Holidays.” The advocacy group #cut50, which aims to slash the incarcerated population in half, had organized the series, where participants urged Obama to commute as many sentences as possible in the remaining weeks of his presidency.

Clemency applicants have long understood that the end of Obama’s second term would be a race against time. But with Trump headed for the White House, it has become an emergency. “I do think that this administration has to pull out all the stops to ensure that every single prisoner who is deemed to meet the criteria is considered and granted clemency,” said Mary Price, general counsel at Families Against Mandatory Minimums.

In Washington, Williams joined other relatives with incarcerated loved ones, as well as people whose sentences had been commuted under Obama’s clemency initiative. At a candlelight vigil at the While House on Monday, Williams stood alongside Barren’s partner, Anrica Caldwell, who recently wrote about his case for The Influence, a website that has published powerful profiles of people seeking clemency. In her piece, Caldwell described how it felt to get her hopes up with every round of commutations. “At these moments I often ask myself, ‘Will he become that lucky person to come home, or will I have to visit him in prison until the day he dies?’” For both Williams and Caldwell, being around others in the same position was a reminder that they were not alone. “It was a rough week for me,” Williams said. “It brought back that hope.”

CNN commentator and #cut50 co-founder Van Jones speaks during a candlelight vigil outside the White House in Washington, D.C., on Nov. 14, 2016.

Photo: Derek Parks

There has been much to criticize about Obama’s clemency effort — from its late start to the paltry number of commutations to date, to the strict conditions it places on those seeking freedom. The White House boasts that Obama has commuted more sentences than the 11 previous presidents combined, yet as of November 6, the number of successful clemency petitions stood at just 944. By contrast, 13,885 petitions have been denied, a rejection rate of well over 90 percent. In October, a man in federal prison declined to accept Obama’s clemency offer, reportedly because of the requirement that he enter a drug treatment program, a stipulation that reformers have criticized. What’s more, in the scheme of our vast national prison landscape, the impact of Obama’s clemency initiative can look pitiful. Federal prisons hold a small fraction of all people behind bars in the United States. Even if the president were to commute every federal sentence in the country, this would put hardly a dent in mass incarceration.

Yet the clemency initiative offers one of very few means for Obama to preserve some shred of his legacy on criminal justice reform. Although his accomplishments in this area have been relatively modest, he was the first sitting president ever to visit a prison — an act that sent a powerful, overdue message to incarcerated people and their families. Under Obama, the Department of Justice has worked with formerly incarcerated leaders to help design programs to expand prison education and address needs of children with incarcerated parents. With a Trump presidency likely to crush such achievements, an aggressive clemency push by Obama could have lasting impact.

“We’ve been working furiously for months now as we saw the end of the administration nearing — there’s a countdown clock on our website,” says Cynthia Roseberry, the project director of Clemency Project 2014, which has processed thousands of applications to date. Although Roseberry is well aware that the number of successful petitions under Obama could have been higher, the figures don’t tell the whole story. “At the end of the day,” Roseberry says, “we did reunite some families. And for some families it meant having somebody home who they thought was going to die in prison.”

Barren’s family is still hoping for this outcome. When he went to prison, “David was a single father raising three boys,” says Williams. He has three daughters, too, and grandparents in their 80s who visit him almost every weekend. The constellation of relatives is a reminder of the effect even one commutation can have. Clemency for Barren would bring relief not just to him, but to a small universe of people.

On November 15, as the press speculated about Trump’s pick for attorney general, a crowd of people gathered outside the Department of Justice. It was the morning after the White House vigil, and activists with #cut50 had organized a press conference urging the president to accelerate his clemency grants. Standing behind stacks of boxes filled with petitions, Van Jones, the group’s co-founder, announced that more than 2 million people had contributed signatures calling on Obama to send people home for the holidays. A young woman pleaded on behalf of her father in prison, “Please Mr. President, if you can, be bold and grant clemency to all of our families and to us, because we are also serving these life sentences with our parents.”

Standing with the crowd was Reynolds Wintersmith, who once faced the prospect of dying in prison for nonviolent drug crimes he committed when he was only 19. The Chicago Tribune described how in 2014, after two decades behind bars, Wintersmith heard his name over the loudspeaker at the Pekin Federal Correctional Institution in Illinois. He discovered shortly afterward that he was going home. “At that moment,” he told me over the phone, “I could shrug like Atlas never did.”

Wintersmith was not focusing on the election results. For one thing, he was unable to vote: “I’m a convicted felon on supervised release,” he said. But more importantly, he sees the current moment as an opportunity to “redefine what needs to be done.” He wants to organize more clemency recipients like himself — the “experts of experience,” as he put it — to get involved in the issue. And he wants to push for broadening the public imagination of what is possible.

He told me about an exchange he had with former Department of Justice Pardon Attorney Deborah Leff. In a meeting with clemency recipients last year, she asked for names of applicants whom they felt deserved clemency too. “Everybody had their long list of names,” Wintersmith recalled. But he didn’t. Later she called on him. “She said, ‘You’ve been really quiet. Do you have anything to say?’ I said, ‘I have a lot to say. I have a list of names of people I would like to see come home. But there are even more people who I’ve never met. To give a list of names would exclude too many people.’”

Over email, Leff declined to discuss the clemency process at Justice. But earlier this year, she sent a resignation letter to her boss, Deputy Attorney General Sally Yates, that stands as a grim indictment of the administration’s priorities in carrying out the initiative. Without enough attorneys and staff to review the nearly 10,000 clemency petitions on her desk, Leff wrote, “the requests of thousands of petitioners seeking justice will go unheard.”

Some of the practical challenges that have slowed the clemency initiative are actually the product of the program’s rigidly limited scope: The more conditions placed on clemency requests, for instance, the more work it takes to ensure that an applicant is eligible. Roseberry pointed out that it took a long time for the DOJ to announce the criteria for its clemency initiative. Then it turned out that the bar was set very high. Not only were petitions limited to “nonviolent, low-level offenders,” but applicants had to have “no history of violence” — even as juveniles. Attorneys tasked with vetting these requests, said Roseberry, often have to dig up files that are decades old and not necessarily available electronically. “You’re talking about 20- to 30-year-old records.”

People hold signs as they participate in the delivery of Change.org clemency petitions to the Department of Justice in Washington, D.C., on Nov. 15, 2016.

Photo: Derek Parks

On the morning after the press conference in front of the DOJ, Veda Ajamu was at a Hilton Garden Inn in D.C., preparing for a meeting with her local congressman, Rep. Steve Cohen of Memphis. She had traveled from Tennessee on behalf of her younger brother, Robert Shipp, who was sentenced to life without parole on cocaine charges in 1994, when he was in his early 20s. Today he is 44 and living in a medium-security penitentiary in Illinois.

Shipp had no previous criminal record when he got involved in a drug conspiracy in Chicago over the course of five months. As Ajamu writes in a Change.org petition, the judge in his case “repeatedly verbalized his objections to the sentence that he was forced to give Robert,” explaining that his hands were bound by federal guidelines that prevented him from exercising discretion. In a pleading letter to the White House on November 6, Shipp himself noted that this same judge had submitted a letter in support of his clemency petition. While he took responsibility for his actions, he wrote that he was not the same person he was in his 20s. Today, he has completed dozens of courses, recently finishing a yearlong training in Microsoft Business Office: “I am proud to share that I successfully completed this college program with a 4.0 GPA,” he wrote. With a daughter as well as nieces and nephews, he reflected, “I realize now that even more than myself, it is my beautiful and loving family who have been greatly harmed by these 23 years of my incarceration.”

Ajamu was emotional when she described how her brother’s imprisonment had hurt her family, especially her father, who begged her before he died to keep fighting for Shipp, whom the family calls Buster or “Bus.” The vigil and press conference were “wonderful,” she said. “I was able to release, I was able to be around so many other families and I was able to draw strength from that.” As her brother’s primary advocate, she feels enormous pressure to do everything she can to help him. “I wake up with this,” she said. “I go to bed with this. I dream of this.”

Fighting for her brother has brought Ajamu closer to him — he calls her his “twin” and his “lifeline.” During visits, they take pictures in their “signature pose,” with their backs toward one another. “It means is we always have each other’s back,” Ajamu explained.

Shipp was 16 years old when another sibling, his older brother, was stabbed to death in Chicago after intervening in a fight. “It sent him into a tailspin,” Ajamu recalled. “He wasn’t able to cope with everything that was going on.” He was arrested a few years later. In the meantime, their brother’s murderer was caught and sentenced to 20 years, ultimately serving just half that time. It is “unbelievable,” Ajamu wrote in her Change.org petition, that their brother’s murderer was free while Shipp had been sent to die in prison for a nonviolent crime.

In 2015, a change in the U.S. Sentencing Guidelines reduced Shipp’s sentence retroactively to 30 years — a ray of hope. But Ajamu hasn’t slowed down, and she won’t be discouraged by a Trump presidency. “The sense of urgency didn’t just start after the election,” she said. For her, the real urgency is defined not by political circumstances but by the lives of the people around her — people who may not be around to see Shipp come home, even with his shortened sentence. Besides, she said, perhaps even President Trump could be persuaded to grant clemency if he heard from people like her. “Mr. Trump, he’s a father. And he’s human,” she says. “Some may say he doesn’t have a heart. But I’ve got to believe if he heard the stories — if he sat down and talked to these people — I think he would empathize with us.”

With little to lose politically as he prepares to leave office, Obama can be urged to act as boldly as possible. But even if he doesn’t push more clemencies through, families will continue to fight on their own, as they always have. As Anrica Caldwell put it, “Sometimes you want to scream and say, ‘Oh my god, this is not gonna happen.’ But then you take a deep breath and you get back on the horse — and you start galloping.”

We depend on the support of readers like you to help keep our nonprofit newsroom strong and independent. Join Us